The present invention is directed to a one-step reaction to produce 3-phenylisoxazolines and 3-phenylisoxazoles. More particularly, the invention is directed to contacting a benzyl halide and sodium nitrite with an alpha-olefin to provide the isoxazoline or with an acetylene to provide the isoxazole in good yields.
Isoxazolines and isoxazoles have a wide variety of uses. They are useful as intermediates in pharmaceutical applications and application in flavor and fragrance chemistry and as water treatment agents.
The subject compounds are presently formed by synthetic routes which require several steps and difficult operating conditions. For example, the common method of forming 3-phenylisoxazolines involves the initial reaction between benzaldehyde and hydroxylamine hydrochloride to form an oxime. The oxime is treated with an alkali hypochlorite to form the oximochloride which is then reacted with an olefin in the presence of base to provide the phenylisoxazoline. 3-phenylisoxazoles were similarly formed using acetylenes in place of the olefin. A less complex synthesis to provide the subject products is highly desired.